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Key West Family & Kid Friendly Rentals

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248 rentals in Key West.
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Sunrise Suite Key West 2 Bed Rooms 2 Full Baths
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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Living room and balcony
1800 Atlantic Condominiums Key West Florida
1800 Atlantic Condominiums
ATLANTIC PARADISE Condo 1800 Atlantic, shared pool, jacuzi, BBQ, family fun!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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Living area
Backyard and Patio
The Southernmost Point
KEY WEST CASA Large Condo, Truman Annex, Shared Pool, Downtown Key West
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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Patio View
La Brisa Pool
Oceanfront 2 Bedroom 2 Bath Condo Key West Florida
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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Casa Del Sol, a Key West Vacation
Front of Home
Paradise Awaits You! Casa Del Sol
Casa Del Sol, a Key West Vacation (Truman Annex)
Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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Clean Apartment in Old Town Key West (Best Downtown Locations)
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
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AMELIA HOME Spacious Private Home with Private Pool, BBQ Grill + Pet Friendly
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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The Tree House Old Town 2 Bedroom MONTHLY Rental
Rental Home
2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps, Kid friendly
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Casa Cay West ~ Beautiful Tropical House - 2 King Beds! Sleeps 8
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Kid friendly
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Conch Haven Old Town 1/1 MONTHLY Rental
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
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Sunset and Ocean View in Key West's Truman Annex with 2 Bikes and Pool Access
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
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Condo in Old Town Key West's Truman Annex - Pool, Bicycle, Free Parking and WiFi
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, Kid friendly
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Artist Cottage in Truman Annex
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
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Secret Villa II * Old Town: Beautiful Home w/ Private Pool, 2 blocks to Duval!
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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Truman Annex: The Plantation SELF CATERING beautifully landscaped rear patio
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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'LOST SHAKER OF SALT' ~ 3 Bed, 2 Bath Pet Friendly Home with 40' Private Pool
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, Kid friendly
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Attitude Key West (2 Bikes and Wireless Internet)
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
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'Oceanside Oasis' * Kings Pointe: Direct Ocean Views & 3 BR'S
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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Secret Villa I * Old Town with Private Pool, close to Duval!
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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Tom's Chicken Coop: Nice Ocean View, Pool, Renovated, Close to Beach
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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My Condo by the Beach with Ocean View
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, Kid friendly
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Sea Breeze Cottage- in Beautiful Truman Annex
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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Tom's 2000sf Direct Oceanfront Penthouse. Renovated, Heated Pool, Close To Beach
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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Seaside Place Key West FL 5 Bedroom House 4 Baths
Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps, Kid friendly
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Attitude Key West at the Beach, 2 Bikes and Internet, Pool, Whirl Pool, Sauna
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
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Catherine House: A charming Old Town Key West cottage
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, Kid friendly
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Quaint Island Escape Condo w/Spacious Balcony Deck in Beautiful Truman Annex
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, Kid friendly
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Harbour Place 115 in Truman Annex Key West
Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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Boli Townhouse - Luxury Rental in gated Truman Annex
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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William Skelton House - Available Easter Weekend!
Rental Home
6 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps, Kid friendly
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Top Floor Ocean Views from every window Olympic Size Pool-Jacuzzi- Sauna-Tennis
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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Key West Beachfront Luxury 2/2 Condo A212 No Hurricane Damage
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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Azure Morning- Oceanfront, near Marina, Pool & Jacuzzi
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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'CORAL CABANA' ~ Lush Porch Views of the Pool & Gardens, near Golf Course!
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Kid friendly
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Villa Paradiso: A unique mid-town paradise
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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Enjoy More Privacy in a Truman Annex End Unit Townhome
Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps, Kid friendly
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NEWLY RENOVATED ...LAST MINUTE SPECIALS...CHECK DATES
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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Apple of Your Eye in Paradise (Truman Annex)!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, Kid friendly
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Rose Lane Villas - Villa Vista - 2 bedrooms - Downtown Key West
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, Kid friendly
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Duval Square Penthouse: A large, beautiful condo steps from the action
Condo/Apartment
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps, Kid friendly
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'LADY ADMIRAL' ~ Sweet cottage & guest house with private pool off Duval
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Kid friendly
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Ann Street Cottage: A bright and airy home near Duval Street
Rental Home
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps, Kid friendly
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Beach House with Ocean View-No Contact Check-In
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
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Majestic Escape near Duval! Pool, wifi, renovated 2/2 1/2, private courtyard.
Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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'CASA DE VINO' ~ Excellent Price for an Amazing Townhouse with Pool & Tiki!
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Kid friendly
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~$~1,500/wk - Best Deal in Key West - Plus 7 Bikes Included!
Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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Rose Lane Villas - Villa Grande - 3 bedrooms - Downtown Key West
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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Peaceful Setting Amongst The Active Island Life Style
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, Kid friendly
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Lazy River Pool, Enchanting Garden, Old Town Key West, Free WiFi, Bikes & Parkin
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, Kid friendly
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Colony Poolside: A charming bungalow near the historic cemetery
Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
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Key West Vacation Rentals and Condos
Browse through the list of beachfront house rentals in the Florida Keys and you’ll start to feel the warm breeze. You’ll sense the cool sand under your feet and taste the spike of a margarita. Everyone and everything on the island of Key West seems to go at its own pace, which makes it a wondrous vacation destination for families and friends of all ages. House and condo rentals abound – penthouse beach villas on the sandy shoreline, inland cottages in the bustling Old Town district, even fully equipped yachts are available for stay!
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Key West Vacation Rentals and Condos
Browse through the list of beachfront house rentals in the Florida Keys and you’ll start to feel the warm breeze. You’ll sense the cool sand under your feet and taste the spike of a margarita. Everyone and everything on the island of Key West seems to go at its own pace, which makes it a wondrous vacation destination for families and friends of all ages. House and condo rentals abound – penthouse beach villas on the sandy shoreline, inland cottages in the bustling Old Town district, even fully equipped yachts are available for stay!
Where To Rent a Vacation Home in Key West
Vacation rentals in Key West can be found all over town, but knowing what each area offers will help you decide on the perfect place. Condo rentals in Old Town will put you in the center of the action – steps from the famous Duval Street, with numerous restaurants, bars, boutiques, souvenir shops and major attractions. Luxurious, modern house rentals on the beach offer more privacy and relaxation. No matter where you make your home base, if you rent a moped or scooter in Key West, you’ll find it easy to get around without a rental car.
Many House Rentals Near Attractions and Activities For All Ages
Key West vacation rentals scatter the whole island, so you’ll always be close to family fun and adventure. Fury Water Adventures offers jet skis, kayaking, parasailing, boating and some of the best snorkeling and diving excursions you’ll ever find. Fishermen will marvel at the eclectic aquatic life in the crystal-blue waters, while families can take the kids to the Florida Keys Eco-Discovery Center, with interactive and dynamic sea exhibits – all just steps away from the island’s spacious, family-friendly condo rentals. Enjoy the romance of paradise on a sunset dinner cruise to wind down from a busy day on the beach or in town.
Key West Bars and Restaurants
Bustling nightlife and gastronomy surround the house rentals in the Historic Seaport neighborhood. Start your night with frozen daiquiris at the famous Lazy Gecko before moving to the award-winning Italian restaurant La Trattoria on the legendary Duval Street. A visit to Key West wouldn’t be complete without trying the conch fritters. And we recommend you indulge in as many different versions of key lime pie as possible. Parrotheads (you know who you are) should make a beeline to Jimmy Buffet’s Margaritaville Café, where you can order up your very own Cheeseburger in Paradise.
Book a Key West Vacation Rental For Your Next Trip
Vacation rentals in Key West are the perfect way to experience the island like a local. Traipse down Duval Street to take in the culture, enjoy the family-friendly attractions with your children and loved ones and relax on the white-sand beaches with a margarita in hand. Whichever way you vacation, TripAdvisor has the best deals on house rentals, condo rentals, and beach homes in Key West.